CN111635438A - Preparation method and application of polyaryl alkyl modified binuclear platinum (II) complex - Google Patents

Preparation method and application of polyaryl alkyl modified binuclear platinum (II) complex Download PDF

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CN111635438A
CN111635438A CN202010590524.6A CN202010590524A CN111635438A CN 111635438 A CN111635438 A CN 111635438A CN 202010590524 A CN202010590524 A CN 202010590524A CN 111635438 A CN111635438 A CN 111635438A
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complex
platinum
quadruplex
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许翠霞
钱广盛
潘怡
赵强
孟洋
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Jiangsu Second Normal University (jiangsu Institute Of Educational Science Research)
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Abstract

The invention relates to a preparation method and application of polyaromatic hydrocarbon modified binuclear platinum (II) complex for targeted induction and stabilization of human telomere G-quadruplex, wherein the structural general formula is shown as formula (1):
Figure 100004_DEST_PATH_IMAGE002
in the formula (1), the reaction mixture is,
Figure 100004_DEST_PATH_IMAGE004
represents the same platinum complex with a side arm, and the platinum complex with a side arm is one of a formula (2), a formula (3) or a formula (4); the complexes can specifically target human telomere sequences, induce the human telomere sequences to form G-quadruplex structures, and stabilize the structures, wherein the melting point is stable and the temperature is as high as 34.2 +/-1.1 ℃; g-quadruplexesIs an important target molecule of potential anti-tumor drugs and is a hotspot for research of scientists at present; therefore, the complex is a potential antitumor drug taking human telomere G-quadruplex as a target.

Description

Preparation method and application of polyaryl alkyl modified binuclear platinum (II) complex
Technical Field
The invention relates to a preparation method and application of polyaromatic hydrocarbon modified binuclear platinum (II) complex which utilizes supermolecular self-assembly to synthesize human telomere G-quadruplex specific targeting, belonging to the field of biochemistry.
Background
Tumors are serious diseases threatening human health and life seriously, have become the second leading cause of human death, and are one of the major topics drawing attention worldwide in the 21 st century. Since 2009 nobel's prize for physiology or medicine awarded us of three scientists in the united states (elizabeth braekbook, carol grede and jack shaskack) who have a prominent contribution in the field of "how telomeres and telomerase protect chromosomes", people have come to recognize that telomeres are not only associated with structural features and stability of chromosomes, but also affect the life, senescence, death, etc. of cells. Research shows that the discovery of the structure of the nucleic acid G-quadruplex and the disclosure of the relation between the nucleic acid G-quadruplex and cancer by the current biological technology provide important targets for the research of the current anti-tumor drugs. The compound can induce DNA to form a G-quadruplex structure, is specifically combined and stabilized, and is expected to inhibit the growth of tumor cells, thereby achieving the anti-tumor effect. Therefore, the related structural features and biological functions of such nucleic acid secondary structures (G-quadruplexes) have attracted extensive attention from scientists in various fields.
As is well known, platinum antineoplastic drugs are the first-line anticancer drugs in clinical treatment, and the success of cisplatin and its derivatives in clinical treatment makes pharmaceutical companies and research institutions invest a lot of manpower, material resources and expenses to support the research of metal complexes as antineoplastic drugs. Meanwhile, the metal complex also has the advantages of simple synthesis steps, rigid-flexible geometric structure change, abundant electrochemical properties, and various performances such as optics, magnetism, catalysis and the like.
The bridged ligand is a series of nitrogen-containing heterocyclic structures with specific aromatic large pi planes, and the purpose of regulating and controlling the size and the rigid/flexible structure of the whole complex can be achieved by changing the substituent of the bridged ligand.
Disclosure of Invention
The invention aims to provide a polyaromatic hydrocarbon modified binuclear platinum (II) complex for target induction and stabilization of human telomere G-quadruplex, aiming at the defects of the prior art, and having a structure shown as a chemical formula (1):
Figure 285972DEST_PATH_IMAGE001
in the formula (1), the reaction mixture is,
Figure 639593DEST_PATH_IMAGE002
represents the same type of side-arm platinum (II) complex which is independently selected from formula (2), formula (3) or formula (4):
Figure 313151DEST_PATH_IMAGE003
in the formula (1), the reaction mixture is,
Figure 43210DEST_PATH_IMAGE004
represents the same substituent group, and the substituent groups are independently selected from formula (5), formula (6), formula (7) or formula (8):
Figure DEST_PATH_IMAGE005
the invention also provides a preparation method of the organic hybrid polyaromatic hydrocarbon modified binuclear platinum (II) complex, which is an organic hybrid polyaromatic hydrocarbon modified binuclear platinum (II) complex obtained by assembling a side arm platinum (II) complex and a bridging ligand into a binuclear structure by utilizing supermolecular self-assembly. The side arm platinum (II) complex is a side arm platinum (II) complex with chloride ions substituted by nitrate radicals or water molecules. The side-arm platinum (II) complex is one of a formula (2), a formula (3) or a formula (4). Said
Figure 853034DEST_PATH_IMAGE006
Represents that the same substituent is one of formula (5), formula (6), formula (7) or formula (8).
The method specifically comprises the following reaction steps: dissolving the platinum (II) complex coordinated by the original chloride ion on a proper amount of DMF (dimethyl formamide), and adding AgNO3Ortho-chloride coordinated sidearm platinum (II) complexes with AgNO3The amount ratio of the substances is 0.9-1:1-1.1, the temperature is programmed to 60-150 ℃, and the reaction is carried out under the condition of N2And (4) reacting for 1-4 days in a dark place under protection, centrifuging by using a low-temperature centrifuge, discarding a precipitate, and keeping clear liquid. Adding bridging ligand into the clear liquid, the mass ratio of the side arm platinum (II) complex coordinated by the original chloride ion to the bridging ligand is 1-2:1, heating to 50-150 deg.C, and adding N2Reacting in dark for 2-6 days under protection, filtering the reaction solution with absorbent cotton after the reaction to obtain clear bright yellow solution (i.e. polyaryl modified binuclear platinum (II) complex solution), weighing excessive NH4PF6Adding into the above solution, adding NH4PF6The mass ratio of the double-core platinum (II) complex solution modified by polyaryl alkyl is 3-8:1, and a large amount of white precipitate appears immediately. Stirring at normal temperature and in dark place for about 20 min, filtering under reduced pressure, washing with glacial ethanol for 2-3 times, drying and centrifuging the obtained product in a vacuum drying oven to obtain light-colored solid matter, namely the polyaryl modified binuclear platinum (II) complex.
This reaction process can be represented by the following reaction formula:
Figure 377556DEST_PATH_IMAGE007
the polyaryl modified binuclear platinum (II) complex provided by the invention can be used as a G-quadruplex stabilizer, and is a potential antitumor drug taking nucleic acid as a target.
The invention synthesizes organic hybrid polyaromatic hydrocarbon modified binuclear platinum (II) complex by a supermolecular self-assembly method, specifically targets human telomere (hTiel) sequence, induces the formation and stabilizes G-quadruplex, and can be used as a G-quadruplex stabilizer, namely a potential antitumor drug.
Compared with the prior art, the invention has the following beneficial effects:
the invention uses easily obtained K with rich sources2PtCl4The series of side arm platinum (II) complexes are synthesized as shown in formula (2), formula (3) or formula (4), and a series of polyaromatic hydrocarbon modified binuclear Pt (II) complexes are synthesized and characterized by a supermolecular self-assembly method with corresponding bridging ligands. Data obtained by FRET screening of human plasmid sequences (hTie), promoter region sequences (c-myc, c-kit and bcl2) and double-stranded (duplex) DNA indicate that the complexes all have excellent sequence selectivity.
Drawings
FIG. 1, FRET melting point curve of dinuclear platinum (II) complex interacting with human telomere sequence (hTel);
FIG. 2, FRET melting point curve for the interaction of binuclear platinum (II) complexes with the promoter region sequence (c-myc);
FIG. 3, FRET melting point curve of dinuclear platinum (II) complex interaction with promoter region sequence (c-kit);
FIG. 4, FRET melting point curve of dinuclear platinum (II) complex interaction with promoter region sequence (bcl 2);
FIG. 5 FRET melting point curves for the interaction of dinuclear platinum (II) complexes with double-stranded (duplex) DNA.
Detailed Description
The technical solution of the present invention is further illustrated by the following specific examples.
Example 1
Synthesizing an organic hybrid polyaromatic hydrocarbon modified binuclear platinum (II) complex with a side arm platinum (II) complex formula (2) and a bridging ligand as a formula (5):
Figure 183750DEST_PATH_IMAGE008
weighing a side-arm platinum complex formula (2) (92.2 mg, 0.2 mmol) coordinated by chloride ions, dissolving in 15 mL of DMF solvent, adding AgNO3(34 mg,0.2 mmol)N2Under the protection condition, the temperature is programmed to 100 ℃, the mixture is heated, protected from light and stirred for about 26 hours, the reaction solution after the reaction is finished is transferred to a high-rotation-speed low-temperature centrifuge (8000 turns, 4 ℃), and AgCl precipitate is removed by centrifugation. Transferring the clear light yellow liquid into a clean reaction bottle, weighing the bridged ligand (5) (47.2 mg, 0.1 mmol) and adding into the reaction system, heating to 120 ℃ by program heating for reaction for 72 h, and reacting with N2And (4) protecting, wherein the whole reaction process is carried out under the condition of keeping out of light. When the bridged ligand (5) completely disappears, the reaction is finished, the reaction is cooled to room temperature, absorbent cotton is used for filtration to obtain clear bright yellow solution (namely polyaryl modified binuclear platinum (II) complex solution), and excessive NH is weighed4PF6Adding into the above solution, adding NH4PF6The mass ratio of the double-core platinum (II) complex solution modified by polyaryl alkyl to the substance of the double-core platinum (II) complex solution is 3-8:1, a large amount of white precipitate appears immediately, the mixture is stirred for about 20 min at normal temperature in a dark place, the mixture is filtered under reduced pressure, the mixture is washed for 2 times by using glacial ethanol, and the obtained product is dried in a vacuum drying oven (0.12 g, 0.77 mmol) with the yield of 77%. Elemental analysis (%): c51H37F12N11O3P2Pt2H2O (theoretical, experimental): c (41.47, 41.02), H (2.95, 2.54), N (9.67, 9.94).
The structural formula of the synthesized organic hybrid polyaryl modified binuclear platinum (II) complex is shown as follows:
Figure 389603DEST_PATH_IMAGE009
example 2
The binuclear platinum (II) complex synthesized in example 1 was used for selective screening experiments and results for different DNA sequences.
Fluorescence Resonance Energy Transfer (FRET):
1. preparing a buffer solution: 60 mM potassium arsenate (KH) was prepared2AsO4) pH =7.4 buffer solution.
2. Preparation of double-labeled DNA samples: double-labeled DNA was human telomer repeat hLabel, c-myc, c-kit, bcl2 and duplex, at concentrations determined by dilution according to the methods described in the commercially available protocols, and annealed at 400 nM in buffer.
3. The binuclear platinum (II) complex was prepared as a 3.0 mM stock solution as described above and diluted with buffer solution to the concentration required for the experiment.
4. Respectively mixing 12.5 mu L of 400 nM double-labeled DNA sample with 12.5 mu L of complex with different concentrations (2 × final concentration), transferring 20 mu L of the mixture into a Roche (LightCycler) PCR tube, standing for 1 hour, testing with a Roche real-time fluorescent quantitative PCR instrument (LightCycler 2 type fluorescent quantitative PCR instrument), fixing the excitation wavelength at 470 nM, correspondingly monitoring the emitted fluorescence intensity at 530 nM, changing the temperature range at 30-100 ℃, increasing the temperature at 1 ℃/min, balancing for 30s after increasing the temperature, sampling,T mthe values are given by the instrument with melting point analysis program; the data plots were obtained by treatment in Origin 8.0 (Origin labcorp.).
5. The above experiments were repeated and the final data are the average of three replicates.
TABLE 1 melting temperature (. DELTA.for binuclear platinum (II) complexes stabilizing different DNA sequencesT m) A change in (c).
Figure 53934DEST_PATH_IMAGE011
As can be seen from the data in Table 1, the synthesized organic hybrid polyaromatic hydrocarbon modified binuclear platinum (II) complex can selectively target human telomere sequence (hTie) to induce the hTie to form G-quadruplex structure and corresponding deltaT mThe value was 34.2. + -. 1.1 ℃. In contrast, the binuclear platinum (II) complex has little stabilizing effect on the sequences of the promoter region (c-myc, c-kit and bcl2) and the double-stranded (duplex) sequence. Research reports that in tumor cells, telomerase activity is activated, and telomerase prolongs telomeres; telomeres in tumor cells are more prone to form G-quadruplex structures than in normal cells. Therefore, the binuclear platinum (II) complex has potential antitumor activity.
The invention uses easily obtained K with rich sources2PtCl4The series of side arm platinum (II) complexes are synthesized as shown in formula (2), formula (3) and formula (4), and a series of polyaromatic hydrocarbon modified binuclear Pt (II) complexes are synthesized and represented by a supermolecular self-assembly method with corresponding bridging ligands; through FRET screening of human telomere sequence (hTie), promoter region sequence (c-myc, c-kit and bcl2) and double-chain (duplex) DNA, obtained data show that the complexes have excellent sequence selectivity, namely, the complexes specifically target the human telomere sequence (hTie) and induce the human telomere sequence to form a G-quadruplex structure, so that the melting point of the complexes is stably increased by about 34.2 ℃; in contrast, such complexes have little stabilizing effect on promoter region sequences (c-myc, c-kit and bcl2) and on double-stranded (duplex) DNA; research reports that in tumor cells, telomerase activity is activated, and telomerase prolongs telomeres; telomeres in tumor cells are more likely to form G-quadruplex structures than in normal cells; therefore, the binuclear platinum (II) complex has potential antitumor activity.
The technical means disclosed in the invention scheme are not limited to the technical means disclosed in the above embodiments, but also include the technical scheme formed by any combination of the above technical features. It should be noted that those skilled in the art can make various improvements and modifications without departing from the principle of the present invention, and such improvements and modifications are also considered to be within the scope of the present invention.

Claims (10)

1. A polyaromatic hydrocarbon modified binuclear platinum (II) complex for target induction and stabilization of human telomere G-quadruplex is characterized by having a structure shown as a chemical formula (1):
Figure DEST_PATH_IMAGE002
2. the polyaromatic hydrocarbon modified dinuclear platinum (II) complex of claim 1, which can induce and stabilize human telomere G-quadruplex in a targeted manner, wherein:
in the formula (1), the reaction mixture is,
Figure DEST_PATH_IMAGE004
independently selected from formula (2), formula (3) or formula (4):
Figure DEST_PATH_IMAGE006
3. the polyaromatic hydrocarbon modified dinuclear platinum (II) complex of claim 1, which can induce and stabilize human telomere G-quadruplex in a targeted manner, wherein:
in the formula (1), the reaction mixture is,
Figure DEST_PATH_IMAGE008
independently selected from formula (5), formula (6), formula (7) or formula (8):
Figure DEST_PATH_IMAGE010
4. a method for preparing the polyaromatic hydrocarbon modified binuclear platinum (II) complex of any one of claims 1 to 3 for the targeted induction and stabilization of human telomere G-quadruplexes, comprising the following reaction steps: pendant platinum (II) complexes coordinating the original chloride ion and AgNO3Dechlorinating the reaction, and adding a bridging ligand to react to obtain the polyaryl modified binuclear platinum (II) complex.
5. The method of claim 4, wherein: the side arm platinum (II) complex coordinated by the original chloride ion and AgNO3The amount ratio of the substances of (a) is 0.9-1: 1-1.1.
6. The method of claim 4, wherein: the mass ratio of the side arm platinum (II) complex coordinated by the original chloride ion to the substance of the bridging ligand is 1-2: 1.
7. The method according to claim 4, wherein the dechlorination treatment comprises the following reaction steps: pendant platinum (II) complexes coordinating the original chloride ion and AgNO3Mixing, heating to 60-150 deg.C under N2And carrying out light-proof reaction for 1-4 days under protection.
8. The method according to claim 4, wherein the step of adding a bridging ligand to the reaction is as follows: adding bridging ligand, heating to 50-150 deg.C under N2And carrying out light-proof reaction for 2-6 days under protection.
9. The use of the polyaromatic hydrocarbon modified binuclear platinum (II) complex according to any one of claims 1-3 for targetedly inducing and stabilizing human telomere G-quadruplex in the preparation of antitumor drugs.
10. Use according to claim 9, characterized in that: the medicament contains pharmaceutically acceptable auxiliary agents.
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CN102898478A (en) * 2012-08-09 2013-01-30 中山大学 High efficiency telomerase inhibitor and application of telomerase inhibitor in antitumor drug
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113341128A (en) * 2021-06-02 2021-09-03 江苏第二师范学院 Biosensor for detecting tobramycin and detection method
CN113341128B (en) * 2021-06-02 2023-05-16 江苏第二师范学院 Biosensor and detection method for detecting tobramycin

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